Disinfectant



Patented Dec. 1942 DISHWFECTANT Vartkes Migrdichian, Greenwich, Conn.,assignor to American Cyanamid Company, New York, N. Y., a corporation-ofMaine No Drawing.

Application December 3, 1940,

Serial No. 368,363

15 Claims.

The present invention relates. to new disinfectants, and moreparticularly to certain organic mercury compounds which are especiallyeffective against plant pests and microorganisms with the result thatthey may be used for all purposes of preserving and disinfecting, forexample, the immunizing of seed grain, the prevention of mildewformation, the preservation of wood, in the preservation of glue and thelike.

These new disinfectants comprise organic derivatives of mercuryrepresented by the general'formula:

Ra Ra in which R1 and R2 denote alkyl or aralkyl radicals, and R3, R4,Ba and Rs denote hydrogen. alkyl, aryl, or aralkyl radicals.

In producing mercury compounds of this type, the acetate salts of saidcompounds are first prepared by the interaction of an alcohol such, forexample, as methyl, ethyl, isopropyl, n-butyl, benzyl alcohol and thelike, a compound containing an ethylenic linkage such, for example, asethylene itself, propylene, isobutylene, styrene and the like, andmercuric acetate.

The acetates thus formed are converted by dilute hydrochloric acid or asodium chloride solution to the corresponding chloride compounds, and bysimple metathesis from the latter and a sodium alcoholate in alcoholicsolution these new products may be readily obtained.

The reactions leading to the formation of ethoxyethyl mercury ethoxide,a typical example of the foregoing compounds, may be illustrated by thefollowing equations:

. CzHr-O-OHr-CHrHg0C|H;+NaCl As showing the wide diversity of compoundswhich may be used for the purposes of this invention, the following maybe mentioned: methoxyethyl mercury ethoxide, methoxyethyl mercurybutoxide, methoxyethyl mercury benzylethyl mercury butoxide,ethoxypropyl mercury ethoxide, ethoxypropyl mercury benzyloxide,methoxybutyl mercury ethoxide, isopropyloxybutyl mercury methoxide andethoxyphenylethyl mercury methoxide.

The above class of mercury compounds possess high fungicidal power andhave been found particularly valuable for use as dusting disinfectantsin combating seed diseases. Excellent control of the fungus diseases ofseed corn may be obtained with dust mixtures containing as low as oneper cent of the active compound. Other plants whose seeds may beadvantageously disinfected in accordance with this invention includerye, oats, barley, maize, wheat, peas, beans, potatoes, etc.

These new disinfectants are also highly efllcacious against plant pestsand microorganisms, such as insects, bacteria, moulds and the like, withthe result that they may be employed for all purposes of preserving ordisinfecting, for example, the immunizing of seeds, the preservation ofwood, the prevention of mildew formation, in the preservation of glue,in insecticidal compositions and the like.

The invention is further illustrated by the following examples:

Emample 1 A dust consisting of one part by weight of the compound,ethoxyethyl: mercury ethoxide (C2H5-OICH2CH2HEOC2H5) and 99 parts byweight of talc is dusted onto seed corn, infected by Fusarium, in theproportion of 1.5 ounces of dust to one bushel of corn. Germination ofthe fungi spores is averted.

Example 2 Benzyloxyethyl mercury butoxide of the formula:

is used in a manner similar to the procedure of Example 1.

Example 3 One gram of dust consisting of 97 parts by weight of talc and3 parts by weight of the mer- 2 2,305,540 eury compound,isopropyioxyethyl mercury in which R1 and R1 are selected from the groupmethoxide consisting of alkyl and aralkyl radicals, and Rs is placed ina stoppered four-ounce bottle. Fifty corn seeds, Gibberella infected,held in a sack suspended in the bottle, are exposed to the vapors w ofthe mercury compound for one week. Upon germination of the exposed seedsit is found that the germination of fungi spores is prevented. v

Example 5 Methoxyethyl mercury ethoxide of the mula:

cm-o-cn1-cm-ng -o c,m

for-

- known.

Although these mercury compounds may be used alone, it is usuallypreferable to mix them with inert fillers or spreading materials such astalc, bentonite, kieselguhr, fullers earth, pumice, silica, silicates,chalk, etc. These inert materials are preferably in a finely dividedstate, as

are the mercury compounds, and mixtures of the ingredients are easilyprepared in any welllmown manner. The proportions of the ingredients inthe finished dust may be varied widely in accordance with the particulareffects desired and the conditions under which they are to be used.Under some circumstances it may be desirable and feasible to apply thepresent compounds in the form of solutions or suspensions in water orother liquid, and the present invention does not preclude such use.

while the invention has been described with particular reference tospecific embodiments, it is to be understood that it is .not to belimited thereto but is to be construed broadly and restricted solely bythe scope of the appended claims.

I claim:

1. The method of protecting organic material subject to attack by plantpests and microorganisms which comprises treating the said materialswith an organic mercury compound of the general formula:

in which R1 and R2 are selected from the group consisting of alkyl andaralkyl radicals, and R3,

and R4 are selected from the group consisting of hydrogen, alkyl, aryland aralkyl radicals.

' v 3. The method of protecting organic materials subject to attack byplant pests and microorganisms which comprises treating the saidmaterials with an organic mercury compound of the general formula:

11 n ai-o-c-t-ng-o-a,

in which R1 and R2 are selected from the group consisting of alkyl andaralkyl radicals.

4. The method of protecting organic materials 1 subject to attack byplant pests and microorganisms which comprises treating the saidmaterials with an organic mercury compound of the gen-' eral formula:

in which R1 is selected from the group consisting of alkyl and aralkylradicals.

5. The method of protecting organic materials subject to attack by plantpests and microorganisms which comprises treating the said materialswith an organic mercury compound of the general formula:

in which R1 is selected from the group consisting of alkyl and aralkylradicals.

'I. The method of immunizing seed whichcomprises treating said seed withan organic mercury compound of the general formula:

in which R1 and R: are selected from the group consisting of alkyl andaralkyl radicals, and Ra, R4, R5 and Re are selected from the groupconsiasltling of hydrogen, alkyl, aryl and aralkyi radic 8. The methodof immunizing seed which comprises treating said seed with an organicmercury compound of the general formula:

in which R1 and R1 are selected from the group consisting of alkyl andaralkyl radicals, and R: and R4 are selected from the group consistingof hydrogen, alkyl, aryl and aralkyl radicals.

9. The method of immunizing seed which comprises treating said seed withan organic mercury compound of the general formula:

in which R1 and R: are selected from the group consisting of alkyl andarallgvl radicals.

10. The method of immunizing seed which comprises treating said seedwith an organic merv cury compound of the general formula:

in which R1 is selected from the group consist ing of alkyl and aralkylradicals.

11. The method of immunizing seed which comprises treating said seedwith an organic mercurycompound of the general formula: y

in which R1 is selected from the group consisting of alkyl and aralkylradicals.

12. The method of immunizing seed which comprises treating said seedwith an organic mercury compound of the general formula:

comprises treating said seed with an organic mercury compound of theformula:

15. The method of immunizing seed which comprises treating said seedwith an organic mercury compoimd of the formula:

